How He Asked

 Getting engaged to a difficult person isn't easy for anyone involved. The Confused Millennial shares her story in getting engaged.


I am just going to come out and say this… I can be difficult.

It's true, most people describe me as “tough”, but when I am screwing up their agenda, I'm difficult.

In 7th grade this label really became a part of me… You see, I hated our class president so I brought her $5.00 for the class field trip in all pennies and nickels… that's right, not even dimes or quarters. The teacher told me I was difficult and refused to accept my money…. and I wonder why I have so many issues with authority… but that's another topic for another day.

Today is all about how he asked in the Wedding Wednesday Series!

…needless to say… I was difficult.

So my fiancé knows me really well, and if you read the post on how met, you probably know a little about the type of woman I am….  I am one nosy mother f*cker and spend most of my days overanalyzing things and trying to figure out the jigsaw puzzles that are life and people.


We did and have done a lot together in the entire planning process. I actually went with him to meet with jewelers when planning my engagement ring. We decided on the jeweler together and I worked with them on my perfect ring… but I wanted the  proposal to be a surprise.

…on a total side note about my ring: we had it shipped from New York, NY, and I actually had to SIGN FOR IT!

Do you know how hard it is to sign for your own engagement ring and not open it?!?

I had to throw the box aside, put on my sneakers and leave our apartment ASAP. I told him that when I got home it better be gone!

… okay back to your proposal…

Obviously I knew we were getting engaged, but seriously had no idea when it would happen. I had recently graduated with my master's degree, fast forward a few months after graduation and I was fired twice in under a month… and at the same time my fiancé was a one man show with his company; totally overworked and underpaid.

Not the best time in either of our lives, when one day my BFF from high school Jenna called me and told me she won some quarterly contest for her company and the prize was an overnight at my favorite spa in Miami, Canyon Ranch (now the Carillon), with massages and mani's for two. She asked if I wanted to go with her and of course I exclaimed “YES!”.


Then I had two weeks to sit, think, and… be difficult. 

I like a very particular massage and couldn't figure out why Jenna was being so weird about letting me call the spa to request certain things. My mind was going a million miles per minute during those two weeks – “How nice is her boss?”, “Why can't I call the spa?”, “What was this contest anyway?” – When I finally walked into our bedroom, looked my fiancé square in the eye, and said,

“IS this you? IS this my proposal? Because that would be f*cking awesome!”

One thing you should know about my fiancé is he is the nicest person I've ever met and is a terrible liar …or so i thought…

He looks at me stunned, then saddened… his face fell as he said:

“I wish… You deserve such an amazing proposal, but honestly I just don't have the time or money to put something like that together right now. I am so sorry.”

The look on his face was so sad and empty that I felt terrible for asking and putting pressure on him. I really let go of the notion that “this was it”.

The morning came and Jenna and I headed down to Miami for our mini get away. I was SO excited! It was November 9th, 2014. In Florida, the joke typically is “if you don't like the weather wait 20 minutes”. Our weather changes in the blink of an eye! No joke, growing up it would be pouring across the street and not a drop over my house or vice versa. Plus November is usually the start of our “dry” season when it rarely rains… but on November 9th, 2014 it was a torrential down pour the entire day. With maybe two or three 30 minute windows of no rain… but we will come back to that.

Jenna and I got our massages, and manicures. I tried this weird goldish matte color that I ended up hating. I couldn't figure out why she and her manicurist (who knew I was getting engaged) kept pushing me to get it changed. The manicurist then told us not to go back into the wet area of the spa because it could result in bubbling of the polish. Since I didn't like my polish I didn't care, and Jenna started getting super weird telling me not to go and she even refused to go back in the jacuzzi or steam because she didn't want to mess up her nails, so I went alone. She kept pushing me that we needed to do our hair and stuff and I was like “I don't care if I go to dinner with wet hair” since I hate blow dryers.


Finally we got back to the room and after 6 hours of massages, jacuzzis, steams, and saunas, I felt like jello. We were supposed to shower, rest for an hour and go to yoga before dinner. After showering I dove into bed and didn't want to move for a year.


Jenna was running around like a crazy person doing her hair and kept telling me to do my hair and make-up. I swear, we've known each other since the age of 14 , and I have never seen Jenna so high maintenance or annoying in my life.  I looked at her like a crazy person and said “but we are going to yoga!” – she told me she wanted to take pictures at this pretty spot I showed her before yoga to get the light (Seriously, who was this person? If I wasn't so tired I would've probably caught on). I kept arguing with her that I didn't want to and we could do it tomorrow or after yoga. Then all 5 ft of Jenna suddenly transformed into Ms. Trunchbull from Matilda


She commanded that I get dressed in my nice dinner outfit and put on make-up right now. I knew I needed to do what she said or there were going to be serious consequences.

… Little did I know, she was panicking because our room had a direct view of the rooftop that Eric was setting the proposal up on. I was so out of it I didn't notice anything as Jenna frantically texted with Eric telling him to get down because I was looking out the window right at him! Meanwhile I was just looking at the ocean haha. Jenna kept panicking as she watched him scurrying around setting everything up and he was texting her and yelling at her to get me out there while we had a 30 minutes break in the rain…

Begrudgingly, I started getting dressed when I realized I forgot nice shoes so I decided to wear my flip-flops… which she started arguing with me over to put on her heels. I had it at that point and refused, telling her to just crop me feet out of the photo.

Like I said… I'm


We made our way over to this gorgeous grassy area on the rooftop overlooking the ocean. This exact spot my fiancé and I had stood almost 5 months earlier. The spot I told him was the perfect place for a proposal. The rain had stopped for just a little, the air felt kind of eerie from the cool winds and the place was a ghost town from the weather. As we start walking I see some guy dressed really nice… I said to Jenna we shouldn't be there and tried to get her to turn back and not interrupt whatever was happening.


She told me “no” and we would ask him to take our photo. I kept protesting for another minute as we were walking when finally my eyes adjusted and I realized it was Eric!

He had candles and rose petals all set up and this was it! I was so confused and overwhelmed all at once that I was squealing and shrieking.

Eric was so nervous you can hear his voice shaking in the videos we have… in fact it was so muggy out that when he went to pull the ring out of his pocket he couldn't and had to double back up to do it.

I declared them both shits and then said “YES!”

brooke images rachel ritlop eric dresdale
Photo cred: Brooke Images


I am so happy to be marrying my best friend. I still can't believe how well he tricked me. Jenna and I always have a good laugh at how demanding she was being and what a brat I was being.


Patience & Stalking: A Millennial Love Story!

How He Asked: A Millennial Engagement Story

5 Ways My Wedding Was Different Than I Imagined

3 Reasons To Have A Long Engagement

9 Fears About Pregnancy [+ Why It’s Okay]

Part of being a good partner is loving yourself!

Grab TCM's positive self talk worksheet!


Do you have a funny proposal story? Would love to hear it in the comments!


18 thoughts on “How He Asked”

  1. I don’t know what you meant on your insta, that was CRAZY romantic. I love it! I love everything about it 🙂

    Laura @

    ps: Here’s to being a difficult lady. People resent us openly about it but secretly love us.

  2. hahahah that is too funny!! I love all of the prefaces. I hear ya girl! Be bossy haha. Sounds like it all turned out perfectly!


  3. This is the CUTEST engagement story!! I was a tad difficult for my engagement too, and asked endless questions and such, while my exasperated husband (then boyfriend) tried with all of his might to get me to the location of the proposal. It makes the story that much better though right? Loving your Wedding Wednesdays!

    xo Ashley

Comments are closed.